I asked Olivia to think of the people she considers to be leaders and the qualities she associates with these people, in essence, to describe their impact on their environment and the people in it. She asked whether I meant leaders in “our business” as opposed to leaders in the books that she reads about leaders in other lives and other places. She said: “I’m thinking about the definition of leadership. You know you read all these books about leadership, Good to Great and others and you don’t see many leaders like that in our business. I reference the Good to Great book because I think it said it very well when it said the best leaders are selfless. The best leaders probably often don’t want the job because the best leaders work for the people that work for them and so many people that end up in leadership roles want to be leaders for themselves and that makes them awful leaders. It’s funny; the irony is that the best leaders are the ones that you probably have to force into the role and I think we end up with great leaders by exception in our business because we often use the wrong criteria to select our leaders. This is a bit of a gender issue for me. The thump your chest folks that end up in senior positions, and I think the investment business is particularly prone to selecting this type of leader which is why women struggle in the business so badly, are painful leaders. Leadership is all about giving not taking. It’s just like being a good parent. Leadership and good parenting, you know, when you read about these two things I don’t see them being a lot different actually”.

Olivia continued: “You need a great leader at the very top of the organization because leadership has to filter down. It gets killed if it is midway through the organization. Leadership is about making tough decisions, not popular decisions, thinking ahead, not being swayed by public opinion. In the case of a CEO of a public company, not being geared in your decision making by what the analysts think; they’re not running the business. You’ve got to be able to struggle through short term performance issues because the things that matter take a long time to sort themselves out and so leadership really does take internal courage. You have to be able to see things through to a good result without the short term rewards or any real evidence that everything will work out and the same thing with sitting atop a team. People wonder what you’re doing or doubt what you’re doing or they only see their piece of things. You have to resist the temptation to please secular interests and see it through to the long term conclusion. The business world we operate in today doesn’t allow you to do that very easily”.

“People that go with the flow because they’re trying to do what’s popular or what appears to be, on the surface, right, that’s bad leadership. Leadership is really hard and it’s lonely. I am friends with my team but I’m a friend on a different level. Your position is isolating. I think it’s easier for women to do this, to stand a little apart. In a way, it’s back to the mothering thing again”. And I asked Olivia whether she was used to the role from being a mother and she said: “Yes, I think they’re very complimentary”.

Difficulties and Obstacles

I asked Olivia to think of the people she had had the greatest difficulty with and how she would characterize them and their impact on their environment and the people around them. She referenced a fellow who ran a business that should have worked hand in hand with hers. He was a guy who wanted to run everything and so he wanted to eliminate everybody on the way through that he thought was either going to be competition for him or was trying to eat some of his lunch. In essence, it was only about him. She says: “As a result, every small decision I ever made I had a completely different moral compass or set of objectives from him; it was just like oil and water and I was expected to be partners with him but I had no common ideology at all. Those are really difficult situations because it’s day in, day out conflict, a terrible situation and, you know, it’s about personalities not business. I’m an “out there” person. If it needs to be said I’m going to say it; I can deal with it. This guy, I don’t know what the personality type is but nothing was what it seemed. He said one thing but there was a whole other thing going on in the background. You never got at it, so nothing ever got worked out. There was all this backroom dealing and it was so complicated. It was just like, oh my G-d, way too complicated. And it went on for seven years. In the end, there were lots of losses for the business as a result of that behaviour and of course when that’s happening at a senior level it goes all the way down into the organization. Those are hard things”.

I asked Olivia about what she considered to be the major obstacles she had faced. And what she did when she faced them, where she turned for support and what she had learned from these experiences. She said there had been different obstacles at different stages of her career and in her experience a woman goes through stages. For example, the obstacles she faces when she is younger and has a young family are different from those she will face later in her career. She says she thinks one of the major obstacles is simply never feeling like you’re doing anything right on any front. “There’s the tug at work where you feel guilty about not being at home and when you’re at home you feel guilty about not working as hard as you could. It’s that feeling of never being at peace, which I think you grow out of. I mean, you get over it, but that was an obstacle earlier on, being a woman knowing that the guys went home and they had all this infrastructure to support them. Women just run around trying to be everything to everyone. I had three kids and this very demanding job and the best support system I had was my husband. We decided early on – I tell this to young women all the time – you can’t both be travelling in the fast lane at the same time. If you don’t have kids you can but if you want to have a family you have to work it out together so that one of you is always going to be the primary one taking the load at home. We never had both of us going crazy in our jobs at the same time once we had children. It just so happened I ended up in the fast lane with my last job. I said it was my turn 10 years ago to get out of the house and back on the fast track and my husband was fabulous about it. It was just like when I said I want to go back to Toronto. He said, okay, we’ll do that. It’s your turn. He’s always been on the board at the school and managed all the kid’s sports activities because I couldn’t be very involved. In fact, he has introduced me to a lot of my good friends because, of course, I wasn’t at the school to meet a lot of them. He got me connected to them which has really made our lives work at this stage. I look back and say, G-d, if he hadn’t done all of this, we wouldn’t have the same quality of life. We wouldn’t have known the kids teachers or be involved in that part of our community, so it’s really important to have one of you helping the other one out. So, he’s my hero. Probably he’s the real hero of this story”.

What Strikes Me?

Leadership is all about giving not taking.

Great leadership and great parenting/mothering are similar. They both require selfless behaviour and can be isolating

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Leadership can be really hard because it’s lonely. You can’t fraternize with your team or have real friendships

To have a real positive and significant impact on any organization, leadership must occur at the very top of the house because it has to filter down through all levels of the organization. Good leaders mid way through an organization find it difficult to survive, let alone thrive, if they are not supported by those at the very top

It’s easier for women to handle the isolation of leadership because they are not part of the fraternity anyway